Oakland Vacations from $415
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
$505
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,678 reviews)
I appreciate that hotel honored their word and also waived the valet fee for two nights for inconvenience. That was appreciated. The price that is charged for parking is almost 1/3 of the price of room. The beds are very uncomfortable and the facility needs an update.
Reviewed on Aug 10, 2026
Stay Pittsburgh
Downtown Pittsburgh
$551
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (314 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.
Reviewed on Aug 9, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.
Mount Washington
Restaurant Row and scenic leafy parks lie along the ridge of a famous hill, where George Washington mapped the terrain for the British.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$119 nightly
$136 total
Aug 23 - Aug 24
Total with taxes and fees
9/10 Wonderful! (864 reviews)
"Overall, the hotel was nice."
Reviewed on Aug 11, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$110 nightly
$125 total
Sep 8 - Sep 9
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
"This Hotel was in a good location and clean. We wish we had more time to stay but for the one night it was just fine. We will try this place again!!!"
Reviewed on Aug 11, 2026
Residence Inn Pittsburgh Oakland/University Place
3341 Forbes Ave Pittsburgh PA
$130 nightly
$148 total
Aug 24 - Aug 25
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"Everything was wonderful"
Reviewed on Aug 10, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Oakland attractions
Carnegie Museum of Natural History
9.2/10 (58 reviews)
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
9.8/10 (7 reviews)
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Cathedral of Learning
9.6/10 (184 reviews)
Take an audio tour and admire the majestic Commons Room and Nationality Rooms in one of the world’s tallest Gothic buildings.
Soldiers and Sailors Memorial Hall and Museum
10.0/10 (1 review)
You can spend an afternoon browsing the exhibits at Soldiers and Sailors Memorial Hall and Museum during your trip to Pittsburgh. Attend a sporting event or visit the shops in this family-friendly area.
Heinz Memorial Chapel
Hosting about 1,000 events per year, this non-sectarian chapel welcomes all and frequently hosts weddings, lectures and concerts as well as religious services.
Petersen Events Center
10.0/10 (3 reviews)
Catch an event at Petersen Events Center during your trip to Pittsburgh. Amble around this vibrant area's riverfront or attend a sporting event.
Carnegie Library of Pittsburgh
8.6/10 (7 reviews)
Carnegie Library of Pittsburgh is just one of the places to see in Pittsburgh, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Pittsburgh Playhouse
You can make plans for a show at Pittsburgh Playhouse during your trip to Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$48
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
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- Visit Downtown Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Strip District Vacations
- Cathedral of Learning
- Pittsburgh Vacations
- Carnegie Mellon University
- North Shore Vacations
- National Aviary
- Acrisure Stadium
- Carnegie Library of Pittsburgh
- Byham Theater
- Carnegie Science Center
- Grandview Overlook
- Andy Warhol Bridge
- Children's Museum of Pittsburgh
- Monongahela Incline
- Senator John Heinz Regional History Centre
- Lighthouse ArtSpace Pittsburgh
- Visit Pittsburgh
- Duquesne Incline
- University of Pittsburgh
- Phipps Conservatory
- Ppg Paints Arena
- Kennywood
- Where to stay in Pittsburgh
- Roberto Clemente Bridge
- Andy Warhol Museum
- Petersen Events Center
- Point State Park
- The Nationality Rooms
- David L Lawrence Convention Center
- U.s. Steel Tower
- Heinz Memorial Chapel
- Soldiers and Sailors Memorial Hall and Museum
- Market Square
- Pnc Park
- Photo Antiquities Museum of Photographic History
- Carnegie Museum of Natural History
- Rachel Carson Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.